Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2401-2407.DOI: 10.6023/cjoc202012011 Previous Articles     Next Articles



李璟奭a, 庄桂林b, 黄强a, 王进义a, 吴亚宇a(), 杜平武a,*   

  1. a 中国科学技术大学化学与材料科学学院 合肥 230026
    b 浙江工业大学化学工程学院 杭州 310032
  • 收稿日期:2020-12-05 修回日期:2021-02-08 发布日期:2021-02-26
  • 通讯作者: 杜平武
  • 基金资助:
    国家重点研发计划(2017YFA0402800); 国家自然科学基金(21971229); 国家自然科学基金(51925206); 国家自然科学基金(U1932214); 浙江省自然科学基金(LR19B010001)

A Conjugated Molecular Crown Containing a Single Pyrenyl Unit: Synthesis, Characterization, and Photophysical Properties

Jingshi Lia, Guilin Zhuangb, Qiang Huanga, Jinyi Wanga, Yayu Wua(), Pingwu Dua   

  1. a Department of Materials Science and Engineering, University of Science and Technology of China, Hefei 230026
    b College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032
  • Received:2020-12-05 Revised:2021-02-08 Published:2021-02-26
  • Contact: Pingwu Du
  • Supported by:
    National Key Research and Development Program of China(2017YFA0402800); National Natural Science Foundation of China(21971229); National Natural Science Foundation of China(51925206); National Natural Science Foundation of China(U1932214); Zhejiang Provincial Natural Science Foundation(LR19B010001)

Macrocyclic π-conjugated materials have attracted much attention due to their unique structures and physical properties. The synthetic methods and physical properties of a π-extended molecular crown containing a single pyrenyl unit, cyclo[7]paraphenylene-2,7-pyrenylene ([7]CPPPy 2,7), were report. This macrocycle was achieved by a rationally designed Suzuki-Miyanra coupling of a curved precursor and pyrene-2,7-bis(boronate), followed by reductive aromatization with stannous acid, and confirmed by various physical characterizations, such as HR-MS and a series of NMR spectroscopies. The photophysical properties of [7]CPPPy2,7 were further studied by UV-vis spectroscopy and other analysis, and its maximum absorption peak was located at 326 nm, which was consistant with density functional theory (DFT) calculations. The fluorescence emission spectrum of [7]CPPPy2,7 was further studied. Under 350 nm excitation, the emission peak appeared at 492 nm. The computational result indicates the strain energy of [7]CPPPy2,7 is as high as 299.17 kJ•mol–1.

Key words: π-conjugated macrocycle, molecular crown, polyaromatic hydrocarbon, pyrene